This portrait--among Bronzino's most arresting--was painted in the 1530s. The sitter is not known, but he must have belonged to Bronzino's close circle of literary friends, which included the historian Benedetto Varchi and the poet Laura Battiferri, both of whom sat for the artist. Bronzino himself composed verses in the style of Petrarch, and some of the fanciful and witty conceits in this picture--the grotesque heads on the table and chair and the masklike face formed by the youth's breeches--would have been much appreciated in literary circles. The book is doubtless a collection of poems.